What I’d say to me back then - Rachel Obstler, EVP of Product at Heap, on why it pays to be picky

Rachel Obstler’s interest in technology started at an early age, leading her to choose MIT when it came to going to university. However, this early interest didn’t translate into an immediate passion for working in technology:

I was always interested in technology, even though I had no idea what I wanted to do with it. If you had asked me what an engineer did when I was in high school, I would have had no clue. I'm not even sure I knew that was a role. It was a long time ago too, so software was not the thing it is today. So I went there and I decided pretty quickly, once I figured out what an engineer was, I didn't really want to do it.

Obstler opted instead to join a consulting firm and then go to business school. However, while at the consulting company, she worked on a project giving out mobile licenses and discovered a fascination with the world of communication. Realising this was going to be a really important growth area, she made a career shift after business school, and joined Lucent Technologies in 1997 as a product manager:

I 'summer-ed' there when I was in business school and that was the first time I tried out product management and I just loved it.

The majority of Obstler’s career from that point has been in product management or adjacent roles, ultimately leading to her current position as EVP of Product at Heap.

Representation 

Around a third of the students on her MIT course back in 1988 were women. Obstler thinks this may have worked in her favor when applying for a place, as the college was actively trying to recruit more women. She also didn’t experience any discouragement from her parents or others about pursuing any particular field of study, including technology:

But there certainly were things that were less encouraging of women that I experienced. I remember one of the math teachers, if he called on you to answer a question and you didn't know the answer, he would say, ‘That's okay, you're a girl’. At the time I thought, 'Good, I'm off the hook'. But in retrospect, how ridiculous.

While MIT was actively trying to attract more women to increase the numbers from around a third, even that proportion seems enviable by today’s standards, where the average ratio for the tech sector is closer to 80/20 male/female. Obstler’s team at Heap is currently bucking that trend.  When she joined Heap, her team was only three people and while it’s still only 10 or 11 people, crucially, that small team has a 50/50 balance. This has been achieved by always being very conscious of encouraging and having diversity, Obstler says.

One key piece is ensuring diversity is built into the recruitment process, she advises. When working with recruiters, Heap requires they put forward diverse candidates: 

It's also about making sure that you're thoughtful about your interview process and that you're not disingenuous about it, but that you show the diversity the team has. I've talked to many women who have interviewed at companies who say diversity is really important and they're really focused on increasing the percentage of women at the company, but then everyone in their interview panel is a man.

They come away from that feeling - I don't want to be the change, I want you to have change, it can't just depend on me, I can't be the token. I need to see you're putting your money where your mouth is.

While Heap was already in a decent place regarding gender balance when Obstler joined the firm, she advised that it still requires work to ensure it continues in that direction.

Heap as a company is invested in this. The power of diversity and creating an inclusive environment is part of Heap's values. It's not an uphill battle  - as in I don't have to convince leadership that it's important -  but that doesn't mean it isn't an ongoing effort. Different people communicate differently. You have to constantly think about how to create an environment where people feel comfortable, that there is trust, that they feel comfortable sharing their opinions. Even if it is totally supported, it doesn't mean that you still don't have to put effort into it every day.

When Obstler joined PagerDuty in 2016, prior to her role at Heap, the team was about 25 percent women. Over the four years she worked there, they raised it to roughly 50% women, helped by a women's Employee Resource Group (ERG). Obstler recalls: 

One of the things the women's ERG did, is it sponsored making sure that other women were trained on interviewing. Just making sure that you have representation of your company in the interview loop so that the candidate gets the most accurate and best representation of what the company actually looks like.

Advice

For companies wanting to improve their gender balance, Obstler advises setting reasonable goals. She gives the example that if you have a team of 10 people - two women and eight men - and the plan is to hire five people over the next year, if three are women and two men, that becomes a ratio of five to 10: 

So maybe you set a goal of getting to 33% by the end of this year, and over the next year up to 40%. You set goals every year and you measure it and you're accountable to them. That's something I did at my last company, it's something we do at my current company.

Since she first joined the tech sector back in the 1990s, Obstler says the biggest change she sees is much more focus on the value of diversity and in creating inclusive cultures. There's a lot more awareness in education, and many more programs helping people understand when they have unconscious bias and training around this.

But those percentages have not really changed that much. It's a really interesting dichotomy that there's a lot more awareness, a lot more focus, but there's still a lot of unconscious bias out there that's limiting growth.

So what advice would Obstler give her younger self coming into the technology business after 25 years of experience?: 

The thing I would tell myself is, if you’re looking for a new role, it's okay to be really picky about it. You think about what you want out of a role – maybe you want to be working at a company where you really believe in the mission, or you have a great manager who is going to develop you or you want to be at a high growth organization. A lot of times you end up finding opportunities where you have to trade off between these things.

My advice to myself would be - don't trade off. Decide what those things are that you want, and keep looking until you find the opportunity that actually can provide all of them. Because you can find a great company with a great manager with a great product, whatever the greats are that are important to you.